Sodium Iodide → Diethyl 2-[(iodoacetyl)amino]malonate

HRID 1707003Notes

Reaction equation

HRID 1707003 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:11][C:12](=[O:15])[CH2:13]Cl)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[I-:17].[Na+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([NH:11][C:12](=[O:15])[CH2:13][I:17])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 243559Diethyl (2-chloroacetamido)propanedioate

Product 1

HCID 15096465Diethyl 2-[(iodoacetyl)amino]malonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5.02 g (0.02 mole) of (2-chloroacetamido)-malonic acid diethyl ester [see Ajay Kumar Bose, J.Indian Chem. Soc. 31, 108-110 (1954)] and 4.50 g (0.03 mole) of sodium iodide in 100 ml of acetone is refluxed for 30 minutes. The reaction mixture is thereupon concentrated in vacuo. Water is added to the residue, and extraction is performed twice with methylene chloride. The organic phase is washed once with diluted aqueous sodium bisulphite solution and twice with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo. The residue is recrystallised from methylene chloride/hexane. After filtration with suction and drying in vacuo, there is obtained (2-iodoacetamido)-malonic acid diethyl ester, m.p. 95°-97°.

Workup

  1. concentrationThe reaction mixture is thereupon concentrated in vacuo
  2. additionWater is added to the residue, and extraction
  3. washThe organic phase is washed once with diluted aqueous sodium bisulphite solution and twice with saturated sodium chloride solution
  4. dry with materialit is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is recrystallised from methylene chloride/hexane
  7. filtrationAfter filtration with suction
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-54c932849c784661a9b98e22f3816d36
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

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